A new route for the expedient synthesis of specific regioisomer of quinazolinone- and phenanthridine-fused heterocycles through a palladium-catalyzed regioselective intramolecular oxidative C-H amination from cyclic strained amides of aromatic amido-amidine systems (quinazolinones) has been developed. The amine functionalization of an aromatic C-H bond from a strained amide nitrogen involved in aromaticity has been a challenging work so far. The fusion of two heterocyclic cores, quinazolinone and phenanthridine, can occur in two different ways (linear and angular), but under the conditions reported here, only linear type isomer is exclusively produced. This approach provides a variety of substituted quinazolinone- and phenanthridine-fused derivatives in moderate to excellent yields. Moreover, such fused molecules show excellent fluorescent properties and have great potential to be a new type of fluorophores for the use in medicinal and material science.
Fluorescent
active small molecules for organelle-specific bioimaging
are in great demand. We synthesized 20 different pyrido–imidazo–indole
fused heterocycles (6–5–5–6 ring) via copper
catalyzed tandem N-arylation reaction in moderate to good yields.
Due to decent fluorescent property, lysosome-directing moieties were
attached on two of these heterocycles. Delightfully, those molecules
tracked lysosome with bright blue fluorescence and colocalized with
a known lysosome marker (Lysotracker Red) in human/murine cells. Therefore,
it may be considered as a rapid (10 min) lysosome staining probe.
We report a palladium‐catalyzed method for the direct synthesis of phenanthridones from benzamides in a single step. Unlike previous reports, the current protocol does not need any directing groups or any harsh conditions. This methodology has a wide functional group tolerance therefore a series of phenanthridones were synthesized with a yield up to 87 %. The efficacy of this protocol was further explored by synthesizing some important naturally occurring amaryllidaceae alkaloids in a single step with very good yields.
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